Preview:

What does Augusta National have in common with your retirement plan? A lot more than you think. Ryan uses the game of golf—and the iconic Masters tournament—as a powerful metaphor for achieving retirement success.

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More About This Episode:

We drive into key takeaways, like why consistency leads to better retirement results, as opposed to risking it all for a “hole-in-one,” and how diversification is just like using a full set of clubs.

Just like in golf, a disciplined approach to retirement planning often yields the best results. From avoiding hazards to staying consistent and playing the long game, we explore how a strategic approach can protect your financial future and keep your legacy intact.

Here’s what we cover in this episode:

🏌️‍♂️ Chasing “hole-in-one” hot stocks won’t win retirement

🧰 You need a full set of clubs – Diversify your investments & tax strategies

⚠️ Avoid the hazards – Taxes, inflation, and healthcare costs can derail your plan

🧠 Your advisor is your caddy guiding you through tough shots with clarity

 

0:00 – Intro

1:19 – The “Hole-in-One” and Retirement Planning

4:11 – The Importance of a Diversified Portfolio

7:46 – Navigating Hazards in Retirement Planning

9:49 – What To Do When You Can’t Avoid Hazards

11:07 – Finish Strong and Adjust the Plan

12:38 –Financial Advisor as a Coach


Resources:

Retire Pilots – https://retirepilots.com

Get your FREE Retirement Toolkit – https://bit.ly/3ZmZsaX

Pilot Tax – https://pilot-tax.com/

The Pilot’s Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Connect with Pilot-Tax: https://pilot-tax.com/

Episode Transcription:

(Note, this is an automated transcription. Please forgive any errors.)

Walter Storholt 

You know the Masters, it’s a beautiful reminder of just how much strategy, patience and long term focus goes in a great round of golf in order to experience success. Well, it turns out that retirement works much in the same way. Today, with the Masters on the doorstep, we’re going to key up a few lessons from the course and talk about how they translate well to your financial life and to preparing for retirement. This should be fun. Let’s dive in back for another episode of the pilots advisor Walter storholtz alongside Ryan Fleming and Ryan I’m looking forward to today’s episode. We get to talk about golf a little bit, the masters. It’s here. Are you excited.

Ryan Fleming 

I’m excited for the Masters. I enjoy watching it, but I am not a good golfer. I’ve given up on that game. I’ve tried, but it’s just, I think I was, I grew up on the other side of the tracks and never really sniffed a country club, and it’s caught, you know, I never was able to catch back up.

Walter Storholt 

Yeah, I’ve tried, but, yeah, pretty terrible myself. I like going to the driving range, but the full rounds is just, it’s a lot. Takes a big chunk out of your day. I guess that’s what some people like about it, though, right?

Ryan Fleming 

Yeah. I mean, if it’s a good getaway, you get outside, get some steps in. But, you know, I’ve, I’ve young kids and so, yeah, to take that much time, it’s just not, not in the cards right now.

Walter Storholt 

Yeah. Well, we can still be golf fans, though, and enjoy watching the sport, especially the masters. Even somebody not into golf, I think, can get enjoyment out of just watching the Masters, absorbing all of the excitement out of that. So as we kind of prepare to maybe absorb a little bit of that over the next couple of weeks, we are going to bring some of these retirement planning lessons to life from the world of golf. So here we go. First lesson, I think, that we can learn here is that a hole in one doesn’t win the tournament. And I have a little bit of Tournament history for you in relation to the masters that ties into this nicely. Ryan, there have been 34 holes in one in masters history. 24 of them came on hole 16, which is known as red bud, no player. And this is the interesting part, no player has ever gone on to win the tournament in the same year they made a hole in one. What kind of sense do you make out of that in the finance side? Oh,

Ryan Fleming 

well, the first thing I think of when I think of a hole in one, I almost think like it’s swinging for the fences, you know, like in baseball, hitting that home run. So I would look at that as, you know, chasing that one stock, getting that big stock pick, or that crypto, and I would venture to say that most people that are doing that have the least amount of success. So I don’t think that going for that hole in one is going to be lead to long term success in Investing. Investing, it’s a lot more about being consistent. You know, consistently keeping your emotions in check, playing the long term game, not making short term emotional decisions and not stock picking. So if you want to get that green jacket in retirement, I would say, stay long term, stay unemotional, stay diversified, and don’t be speculating and gambling with your money by trying to find that that hot stock

Walter Storholt 

pick. Yeah, in fact, in the Masters, a lot of the times, or any golf tournament, people are often faced with that choice of, do I go for the hole in one? But it might be the risky shot. It might be the shot where, if you get it just a little bit wrong, you end up in the sand trap, or, even worse, the water, when there’s options for especially somebody who might be leading that might be well positioned in the tournament standings, maybe if they just lay up a shot, if they just play the safe route, they’re going to withstand that lead and withhold maybe some of the other obstacles that they might have otherwise interact with. So try to make smart decisions, especially if you’re in the lead or ahead really kind of becomes the name of the game well,

Ryan Fleming 

and I would argue that that player that lays up consistently takes this, the more conservative, smarter play, they win championships, you know. And you know, no different than football. Since we have a lot of different sports fans out there, I’ll throw a couple other things in there. There you go, you know, Defense wins championships. Or another thing is, you know, the best hitters in baseball aren’t necessarily the home run hitters, they’re the one that’s consistently hitting, you know, singles and doubles and getting on base. And if you get on base, that’s how you score runs. And I look at investing the same way, just being more consistent. You

Walter Storholt 

bring up an interesting little segue to our second point here, Ryan, and it’s because in football, you just have the football. In basketball, you have the basketball in even in, I don’t know, other other hockey, you’ve got the puck and a stick, not a whole lot of variety in how the game’s being played, not quite the same. In golf, you’ve got a set of golf clubs. You’ve got a whole bunch of different options that you can have in your bag for every scenario that you might face. And so that’s our second lesson, is that you’re going to need a full set of golf clubs to be successful in a tournament like the masters. In fact. Fun fact for you, Augusta National, considered one of the more challenging courses in the world. Very demanding takes creativity and precision to you know, have success there. Interestingly, in 2022 Scotty Scheffler, it was kind of notable that he used every single Club. In his bag in the tournament, including some specialty wedges and fairway woods. And it highlighted how you can’t just go out there with a driver and a putter and expect to win the Masters, although that would be kind of entertaining to watch all those guys make it through the whole course with one with one club.

Ryan Fleming 

That sounds like my kind of golf tournament where we use the driver even on the on the greens, but

Walter Storholt 

yeah, as I think about like, going to play around, I think just walking around with one club would be kind of fun and just, wherever you are, take a whack and just keep walking. And it would be, it’d be fun. Yeah, my

Ryan Fleming 

irons weren’t too bad. I’d probably be better off if I just learned to swing one club and consistently swing that club. That’s a good point. Maybe I should try that my golf game. It might be a little bit better, but, not you know, how do I relate this to finance? You know, you can’t have one trick pony out there. You can’t have just one stock. You know, when we talk about diversification, I’m not just talking stocks or cash, you know, we’re talking about other things that we use to eliminate sequence of returns, risk and retirement or tax planning. It takes the full gamut, but, but I kind of mostly view that as having a diversified portfolio. You know, the more diversified you are, you can actually lower your risk and then increase your return or increase your percentage of winning the the match that day. So I think diversified accounts, different investment accounts, different tax strategies all make up to get to retirement safely, because you want to have you know, more arrows in your quiver for whatever situation or whatever the market’s thrown at you at that point in time. Masters

Walter Storholt 

fans will know that Ray’s Creek winds through amen corner. That’s definitely the kind of notable term for holes, 1112, and 13, often one of the I mean, that’s the area where tournaments are won and lost. Given my understanding of the Masters, a very iconic stretch of the course. It includes a lot of treacherous hazards, at least in terms of, you know the golf world. You know sand traps and the bunkers and water you know water features as well. It has claimed some of the biggest names in masters history who were once leading and then fall behind when they get into that amen corner. In fact, Jordan Spieth, popular golf name, had a quadruple bogey in 20, 2016 at hull 12, classic example of how a single hazard can derail an entire round. I can probably see where you’ll take this one for the retirement plans.

Ryan Fleming 

That’s one thing that is really tough about golf, is yeah, you can get one bad shot, and then next thing you know, you’re, you know, you’re a triple Bogey, or whatever it might was, yeah. And that’s it,

Walter Storholt 

yeah. It’s like, but my cards reading a five, a, six, a, seven, a, five, a, seven and a 30, yeah,

Ryan Fleming 

well, and so many rounds where you just have to be consistent to actually win. I mean, it’s all about consistency, yeah, and when I think about the hazards in retirement, when there’s a ton of hazards in retirement, there’s a ton of hazards in retirement planning, you know, ones that I think of offhand are, you know, taxes for sure, tax surprises, health care costs and retirement continue to go up at unprecedented levels. And then, of course, the one that we deal with almost every year is market downturns. And I think, you know, you could plan for a lot of those things, but the bigger factor is how you react to them. You know, you want to plan for them as much as possible. But I think the hardest part is when you don’t even know it’s out there, don’t see it coming, didn’t plan for it. And you are, you know, entering retirement, you didn’t even take into account inflation or taxes. Well, guess what? You’re in a bad spot at that point in time. So, you know, good, good financial planning is not just aiming, you know, just for the green it’s, it’s looking at all those other hazards and taking that, that more conservative play to make sure we don’t do something that’s going to blow up your whole retirement

Walter Storholt 

plan. Attention aviators, when you’ve spent years in the cockpit managing the complexities of flight, isn’t it time you navigated your retirement with the same precision? Introducing retire pilots.com right at your touchdown zone on our home page, there’s a beacon flashing, get my free tool kit. Click that and you’ll be cleared for a direct route to Ryan’s retirement tool kit, tailor made for pilots like you. Inside, you’ll find two of his important works, the pilot’s advisor and pilots retire early. Between these two books, you can decipher the nine critical decisions when retiring before 65 and discover the seven lessons to help pilots land safely in retirement. But that’s not all. This toolkit is packed with altitude high value, including extras to get your retirement plans off the runway and light the afterburners on your 401 k vector on over to retire pilots.com to grab your toolkit, and let’s embark on this journey together. Yeah, that’s the frustrating part. Is, you know, yes, hitting the hazards is a big issue for people who are trying to hit that hole in one. We talked about that at the beginning of the show. But unfortunately, even when you’re trying to play it safe and trying to do the right thing. Thing these hazards can come up and get you. So to me, it’s still even a golfer who’s not trying to take all those risks. They’ve still got to be aware of the hazards and actively try to avoid them. It doesn’t just magically, you know, don’t just magically avoid them. You’ve got to kind of give them the attention that they deserve in order to move past them

Ryan Fleming 

well, and also know that you got that sand wedge. I mean, if you hit it on the beach, you have that sandwich. So it was something that you prepared for in case it happens.

Walter Storholt 

Okay? So saying you’re not always going to avoid the hazard, sometimes you’re going to end up there, even if you try not to

Ryan Fleming 

exactly. And I look at it, it’s funny. We we engineer and build out these portfolios knowing that the market’s going to have downturns. You know, we know the market goes up and down, but it’s, it’s quite interesting to watch how people react when we actually do have a downturn in the market. You know, 2025 has been a lot of self inflicted with the tariffs and everything, but we knew that we’re going to have a downturn. I mean, we do almost every year. There’s almost a 10% pullback every year. But it’s very interesting to watch how people react when it actually happens. You’re

Walter Storholt 

saying your plans, the portfolios that you build for clients. You’ve got sand wedges in there for when we’re in the bunker like we are right now. Absolutely Okay. Very good. Another lesson from the game of golf and the masters the final holes, well, they’re just as important as the first few. Augusta is famous for its drama on the back nine on Sunday. Think Tiger Woods who stormed from behind in 2019 with the red shirt, and maybe Greg Norman, who lost the other side of the equation. There a six stroke lead in 1996 those final few holes can make or break the tournament, even if you started off really, really well, yeah,

Ryan Fleming 

I think about this. And I think the, you know, in the initial holes, the mistakes that most investors make are actually not taking on enough risk. You know that you need to have an aggressive strategy for most of your working years to grow your money, let your money work for you. But of course, yeah, when you get on the back nine, you know, and whether this is right before retirement, your 70s, 80s, you know, if you’re lucky enough to live to your 90s, well, we got to adjust the plan a little bit. And you know, that starts going into a lot of other things, longevity, risk, Legacy planning. I mean, those come into play long term care. So you don’t want to just plan for the front nine. I mean, you want to know while you’re playing the front nine what’s coming on the back nine. And I think, I think the real, the best golfers in the world have that course pretty memorized, so that they know they might be able to be a little aggressive on a certain hole and maybe win, but not be not willing to give up a stroke on another hole. You know where it could go south, I think, and I think they analyze it that closely. Well,

Walter Storholt 

you bring up a great point that dovetails nicely into our final point here, Ryan, because golfers have the chance to walk the course, to play the course. Year after year after year, they know what to expect, but if somebody goes into retirement, that’s the first and only time they’re really going to walk down that road. And so that’s where the two kind of diverge a little bit. But we can even the score when we think about the concept of a caddy, right? And every pro that you see on tour has a caddy, and the role of the caddy is really iconic at Augusta, of course, with the white the white jumpsuits and everything. In fact, Jack Nicklaus, he credited many of his victories, including his famous 86 win, to the strategic decisions that his caddie helped him make in 2023 John roms caddy, Adam Hayes was praised for helping him manage the conditions, kind of understand what he was facing, and just manage the pressure that he was facing. It down the stretch, all that pressure’s on that golfer and that caddy can step in and help alleviate and relieve some of that. I gotta think in retirement planning, somebody can turn to an advisor who has been down that retirement road many times with other clients and utilize them like a caddy to get through that stretch.

Ryan Fleming 

I think that’s great. I mean, having that caddy there, I mean, or even everybody has a coach, right? Tiger Woods had a hitting coach. Michael Jordan had a coach, whether it was lifting, shooting, it doesn’t matter. Everybody has a coach. It’s

Walter Storholt 

always funny to think about the greatest in the world having coaches, right? Yeah,

Ryan Fleming 

but they need those that outside perspective, per se. And I think one thing that’s really interesting about being a financial advisor is you get to see everyone’s different situations. You get to see when life happens. So you’ve seen a lot of these mistakes that have been made in the past, previously. So you know, you know to try to help somebody get out of those. And I really do, I feel like it’s much more of controlling emotions and being a counselor. I mean, obviously the numbers play into it. Engineering portfolios are a big part of it, but a lot of it is just avoiding mistakes. When I, when I come across a do it yourselfer, I actually feel really bad for them, because I can see just in their emotion and the way they look at things that that it’s going to turn out not the way they want it, you know, because they’re, they’re they’re missing all those other hazards. They’re just looking at one thing. And I, you can tell, and I think one of the biggest ones is just tax planning. I don’t, I can’t tell you how many times I’ve seen somebody that did a fabulous job of saving but all their money’s tax deferred. And I’m like, Well, I guess we’re going to give half of that to the government. So. Yeah, no, I think a good financial advisor is like your retirement caddy. You know, they can help you choose the right club, avoid some of those hazards. And, you know, talking about, like, keeping your eye on the flag, keeping your eye on the prize, regardless of all the distractions around here. Sometimes

Walter Storholt 

it’s psychological, the role that you’re fulfilling Absolutely,

Ryan Fleming 

absolutely, I call, call it talk, you know, talking people off the ledge at times too. So, and it’s tough on me, too. I mean, I yeah, I think it’s very stressful when the market is down and people are overreacting and getting emotional, because it weighs a lot on me, because I do care that much and I don’t. I want them to be able to see how this is just a blip on the radar, and to not make any short term emotional decisions, because people

Walter Storholt 

do, yep, that’s fantastic. Ryan, well, I know we get the question a lot. Is from pilots, hey, well, how do I get started? Where do I begin? I want to get a better financial plan. I want to talk about retirement. I’ve never really put this plan on paper before. I’ve never walked down that line. Or, Hey, you’re talking about some concepts that are new to me, and I need to learn more. What is my tax exposure? These are the kinds of questions that begin to pop up a lot, and we have one place to tell people where to begin, and that’s to get Ryan’s retirement toolkit. It’s a toolkit that includes Ryan’s books. It’s specifically built for pilots with lots of great information that’s going to teach you some of the basics, help you learn a little bit more about the role that Ryan can play in your portfolio as well. It’s a really valuable resource. You can get it for free. All you have to do is go to retire pilots.com We’ve also got it linked in the description of today’s show, so that you can find it easily as well. But that’s the place to begin. Order the toolkit. Get that great information. Start there, and then Ryan will be able to follow up with you with more specifics about your plan, your situation, what you’re going through, and seeing if you can help you in a more one on one way. So go to retire pilots.com to find that toolkit or click the link in the description of today’s show. Ryan, great episode today. Appreciate your help and your guidance, and we’ll have to get out there and work on the golf game at least a little bit. I’m inspired slightly by today’s show. All

Ryan Fleming 

right, it’s going to take a lot more time for me to get good at that game, for sure, but it’s always great doing a podcast with you. Walter, well,

Walter Storholt 

we’ll go to top golf and just have a beer and hit some balls, and that doesn’t really matter at that point. How about now, that’s my style, right there. All right. I love it. Thanks for joining us, everybody. We’ll see you next time on the pilots advisor.

Speaker 1 

Information is for illustrative purposes only and does not constitute tax investment or legal advice. Always consult with a qualified investment legal or tax professional before taking any action. Do.